Cyclohexylamine → 2-Cyclohexylamino-5-nitropyridine

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (60% dispersion in mineral oil, 1.99 g, 49.8 mmol) was washed 3x with hexanes then a solution of cyclohexylamine (3.8 mL, 33.2 mmol) dissolved in tetrahydrofuran (50 mL) was added. After stirring for 30 minutes at 22° C. 2-chloro-5-nitropyridine (5.00 g, 31.5 mmol) was added and the reaction mixture was heated to reflux for 3 hours. The solution was cooled to ambient temperature, quenched with saturated aqueous NH4Cl and concentrated in vacuo. The residue was redissolved in ethyl acetate then washed 2x with saturated NaHCO3, saturated NaCl, dried over anhydrous Na2SO4 and concentrated in vacuo. The product was recovered as a brown oil.

Provenance & Evidence